New method of fluorination using potassium fluoride in ionic liquid: significantly enhanced reactivity of fluoride and improved selectivity

DW Kim, CE Song, DY Chi

Index: Kim, Dong Wook; Song, Choong Eui; Chi, Dae Yoon Journal of the American Chemical Society, 2002 , vol. 124, # 35 p. 10278 - 10279

Full Text: HTML

Citation Number: 204

Abstract

We have found the new nucleophilic fluorination reaction of some halo-and mesylalkanes to the corresponding fluoroalkanes with KF in the presence of [bmim][BF4] under various reaction conditions. 2-(3-Methanesulfonyloxypropoxy) naphthalene (1) was used as a model compound to optimize this fluorination reaction. Whereas the fluorination of the mesylate 1 with KF in an organic solvent such as CH3CN at 100° C occurred hardly even after 24 h, ...

Related Articles:

A new class of SN2 reactions catalyzed by protic solvents: facile fluorination for isotopic labeling of diagnostic molecules

[Kim, Dong Wook; Ahn, Doo-Sik; Oh, Young-Ho; Lee, Sungyul; Kil, Hee Seup; Oh, Seung Jun; Lee, Sang Ju; Kim, Jae Seung; Ryu, Jin Sook; Moon, Dae Hyuk; Chi, Dae Yoon Journal of the American Chemical Society, 2006 , vol. 128, # 50 p. 16394 - 16397]

Polymer-supported protic functionalized ionic liquids for nucleophilic substitution reactions: superior catalytic activity compared to other ionic resins

[Shinde, Sandip S.; Lee, Byoung Se; Chi, Dae Yoon Tetrahedron Letters, 2008 , vol. 49, # 27 p. 4245 - 4248]

Dipyrrolidinomethylaminophosphoric acid triamide (DPMPA) as an activator for the samarium diiodide-mediated reduction of alkyl and aryl halides

[McDonald, Chriss E.; Ramsey, Jeremy R.; Sampsell, David G.; Anderson, Laura A.; Krebs, Jordan E.; Smith, Samantha N. Tetrahedron, 2013 , vol. 69, # 14 p. 2947 - 2953]

A resin-promoted Williamson's alkyl aryl ether synthesis. Methylation of 2-tert-butyl-5-methylphenol with methyl chloride.

[Kato; Kakamu; Shioiri Chemical and Pharmaceutical Bulletin, 1981 , vol. 29, # 8 p. 2246 - 2250]

Cyclizations and rearrangements of samarium diiodide-generated vinyl radicals

[Capella, Laura; Montevecchi, Pier Carlo; Navacchia, Maria Luisa Journal of Organic Chemistry, 1995 , vol. 60, # 23 p. 7424 - 7432]

More Articles...